#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/35/2223538.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223538
loop_
_publ_author_name
'Ali, Farukh Iftakhar'
'Babar, Tariq Mahmood'
'Rama, Nasim Hasan'
'Jones, Peter G.'
_publ_section_title
;
 3-(3-Bromobenzyl)-1H-isochromen-1-one
;
_journal_coeditor_code           RZ2357
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2511
_journal_paper_doi               10.1107/S1600536809037246
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H11 Br O2'
_chemical_formula_moiety         'C16 H11 Br O2'
_chemical_formula_sum            'C16 H11 Br O2'
_chemical_formula_weight         315.16
_chemical_name_systematic
;
3-(3-Bromobenzyl)-1H-isochromen-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.130(6)
_cell_angle_beta                 98.392(7)
_cell_angle_gamma                113.844(8)
_cell_formula_units_Z            2
_cell_length_a                   7.4508(5)
_cell_length_b                   8.1824(6)
_cell_length_c                   11.3663(8)
_cell_measurement_reflns_used    9750
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      30.6551
_cell_measurement_theta_min      2.7198
_cell_volume                     625.58(9)
_computing_cell_refinement
;
CrysAlisPro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlisPro (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlisPro (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Oxford Xcalibur E'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16250
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    3.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Oxford Diffraction 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0203
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0233P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0443
_refine_ls_wR_factor_ref         0.0448
_reflns_number_gt                2899
_reflns_number_total             3449
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2357.cif
_cod_data_source_block           I
_cod_original_cell_volume        625.58(8)
_cod_database_code               2223538
_cod_database_fobs_code          2223538
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.13942(2) 0.205557(19) -0.113746(13) 0.02023(5) Uani d . 1 . .
O O1 0.70881(14) 0.19099(12) 0.46026(8) 0.0146(2) Uani d . 1 . .
O O2 0.78538(15) 0.22208(13) 0.65672(8) 0.0195(2) Uani d . 1 . .
C C1 0.75969(19) 0.29281(17) 0.56653(12) 0.0141(3) Uani d . 1 . .
C C2 0.67678(19) 0.25762(17) 0.35091(11) 0.0128(3) Uani d . 1 . .
C C3 0.69140(19) 0.42394(17) 0.34239(11) 0.0136(3) Uani d . 1 . .
H H3 0.6699 0.4662 0.2661 0.016 Uiso calc R 1 . .
C C4 0.73964(18) 0.54146(17) 0.44789(11) 0.0124(3) Uani d . 1 . .
C C5 0.7521(2) 0.71742(18) 0.44484(12) 0.0170(3) Uani d . 1 . .
H H5 0.7288 0.7643 0.3706 0.020 Uiso calc R 1 . .
C C6 0.7982(2) 0.82214(18) 0.54931(13) 0.0182(3) Uani d . 1 . .
H H6 0.8045 0.9404 0.5465 0.022 Uiso calc R 1 . .
C C7 0.8354(2) 0.75669(19) 0.65887(13) 0.0185(3) Uani d . 1 . .
H H7 0.8683 0.8306 0.7301 0.022 Uiso calc R 1 . .
C C8 0.8248(2) 0.58509(18) 0.66416(12) 0.0162(3) Uani d . 1 . .
H H8 0.8507 0.5406 0.7389 0.019 Uiso calc R 1 . .
C C9 0.77565(19) 0.47639(17) 0.55899(11) 0.0126(3) Uani d . 1 . .
C C10 0.6231(2) 0.11432(17) 0.25339(11) 0.0161(3) Uani d . 1 . .
H H10A 0.4972 0.0138 0.2639 0.019 Uiso calc R 1 . .
H H10B 0.7280 0.0682 0.2602 0.019 Uiso calc R 1 . .
C C11 0.5989(2) 0.17984(17) 0.12982(11) 0.0144(3) Uani d . 1 . .
C C12 0.4136(2) 0.16677(17) 0.07491(11) 0.0146(3) Uani d . 1 . .
H H12 0.3011 0.1147 0.1140 0.018 Uiso calc R 1 . .
C C13 0.39414(19) 0.23009(17) -0.03706(12) 0.0143(3) Uani d . 1 . .
C C14 0.5553(2) 0.30743(18) -0.09635(12) 0.0155(3) Uani d . 1 . .
H H14 0.5401 0.3518 -0.1726 0.019 Uiso calc R 1 . .
C C15 0.7391(2) 0.31864(17) -0.04193(12) 0.0165(3) Uani d . 1 . .
H H15 0.8510 0.3704 -0.0815 0.020 Uiso calc R 1 . .
C C16 0.7613(2) 0.25498(17) 0.06999(12) 0.0157(3) Uani d . 1 . .
H H16 0.8880 0.2627 0.1061 0.019 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C2 . . 122.56(10) ?
O2 C1 O1 . . 117.22(12) ?
O2 C1 C9 . . 126.19(12) ?
O1 C1 C9 . . 116.59(11) ?
C3 C2 O1 . . 121.65(12) ?
C3 C2 C10 . . 128.78(12) ?
O1 C2 C10 . . 109.56(11) ?
C2 C3 C4 . . 120.62(12) ?
C9 C4 C5 . . 118.50(12) ?
C9 C4 C3 . . 118.22(12) ?
C5 C4 C3 . . 123.28(12) ?
C6 C5 C4 . . 120.19(13) ?
C5 C6 C7 . . 120.77(13) ?
C8 C7 C6 . . 120.14(13) ?
C7 C8 C9 . . 119.74(13) ?
C8 C9 C4 . . 120.65(12) ?
C8 C9 C1 . . 119.01(12) ?
C4 C9 C1 . . 120.34(12) ?
C2 C10 C11 . . 112.98(11) ?
C12 C11 C16 . . 119.06(12) ?
C12 C11 C10 . . 120.17(12) ?
C16 C11 C10 . . 120.77(12) ?
C13 C12 C11 . . 119.64(12) ?
C12 C13 C14 . . 121.67(13) ?
C12 C13 Br . . 119.50(10) ?
C14 C13 Br . . 118.81(10) ?
C15 C14 C13 . . 118.52(13) ?
C14 C15 C16 . . 120.63(13) ?
C15 C16 C11 . . 120.46(13) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
C2 C10 H10A . . 109.0 ?
C11 C10 H10A . . 109.0 ?
C2 C10 H10B . . 109.0 ?
C11 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C15 C14 H14 . . 120.7 ?
C13 C14 H14 . . 120.7 ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C15 C16 H16 . . 119.8 ?
C11 C16 H16 . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br C13 . 1.9001(13) ?
O1 C1 . 1.3796(15) ?
O1 C2 . 1.3859(15) ?
O2 C1 . 1.2073(15) ?
C1 C9 . 1.4618(18) ?
C2 C3 . 1.3256(18) ?
C2 C10 . 1.4996(18) ?
C3 C4 . 1.4426(18) ?
C4 C9 . 1.4035(18) ?
C4 C5 . 1.4056(18) ?
C5 C6 . 1.3787(19) ?
C6 C7 . 1.392(2) ?
C7 C8 . 1.3759(19) ?
C8 C9 . 1.3994(18) ?
C10 C11 . 1.5166(18) ?
C11 C12 . 1.3911(18) ?
C11 C16 . 1.3947(19) ?
C12 C13 . 1.3854(18) ?
C13 C14 . 1.3859(19) ?
C14 C15 . 1.3842(18) ?
C15 C16 . 1.3887(18) ?
C3 H3 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C12 H12 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6 O1 1_565 0.95 2.58 3.4666(16) 155.3
C10 H10A O2 2_656 0.99 2.50 3.4685(17) 166.0
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 O1 C1 O2 . . . . -179.57(11) ?
C2 O1 C1 C9 . . . . 0.95(17) ?
C1 O1 C2 C3 . . . . -0.72(19) ?
C1 O1 C2 C10 . . . . -179.69(11) ?
O1 C2 C3 C4 . . . . -0.6(2) ?
C10 C2 C3 C4 . . . . 178.12(13) ?
C2 C3 C4 C9 . . . . 1.66(19) ?
C2 C3 C4 C5 . . . . -178.28(13) ?
C9 C4 C5 C6 . . . . -0.22(19) ?
C3 C4 C5 C6 . . . . 179.72(13) ?
C4 C5 C6 C7 . . . . 0.9(2) ?
C5 C6 C7 C8 . . . . -0.6(2) ?
C6 C7 C8 C9 . . . . -0.2(2) ?
C7 C8 C9 C4 . . . . 0.9(2) ?
C7 C8 C9 C1 . . . . -178.34(13) ?
C5 C4 C9 C8 . . . . -0.63(19) ?
C3 C4 C9 C8 . . . . 179.43(12) ?
C5 C4 C9 C1 . . . . 178.56(12) ?
C3 C4 C9 C1 . . . . -1.38(18) ?
O2 C1 C9 C8 . . . . -0.1(2) ?
O1 C1 C9 C8 . . . . 179.34(11) ?
O2 C1 C9 C4 . . . . -179.30(13) ?
O1 C1 C9 C4 . . . . 0.14(18) ?
C3 C2 C10 C11 . . . . 5.0(2) ?
O1 C2 C10 C11 . . . . -176.15(11) ?
C2 C10 C11 C12 . . . . -90.92(15) ?
C2 C10 C11 C16 . . . . 88.60(15) ?
C16 C11 C12 C13 . . . . -0.72(19) ?
C10 C11 C12 C13 . . . . 178.81(11) ?
C11 C12 C13 C14 . . . . -0.27(19) ?
C11 C12 C13 Br . . . . 178.14(9) ?
C12 C13 C14 C15 . . . . 0.9(2) ?
Br C13 C14 C15 . . . . -177.54(10) ?
C13 C14 C15 C16 . . . . -0.50(19) ?
C14 C15 C16 C11 . . . . -0.5(2) ?
C12 C11 C16 C15 . . . . 1.09(19) ?
C10 C11 C16 C15 . . . . -178.44(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743326
